3,3',5-Triiodo-L-thyronine CAS 6893-02-3
Introduction：Basic information about 3,3',5-Triiodo-L-thyronine CAS 6893-02-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
3,3',5-Triiodo-L-thyronine Basic information
| Product Name: | 3,3',5-Triiodo-L-thyronine |
| Synonyms: | L-Tyrosine, O-(4-hydroxy-3-iodophenyl)-3,5-diiodo- (9CI);NSC 80203;Thyronine, 3,3',5-triiodo-, L- (6CI);IODOTHYRONINE;3,3,5-TRIIODO-L -THYRONINE 95-98% FREE ACID CRYSTALLINE;Liothyronine;O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine;3,3μ,5 Triiodothyronine (T3) |
| CAS: | 6893-02-3 |
| MF: | C15H12I3NO4 |
| MW: | 650.97 |
| EINECS: | 229-999-3 |
| Product Categories: | Stable Isotopes;Inhibitors;Amino Acids & Derivatives;Intermediates & Fine Chemicals;Labeling and Diagnostics Reagents;Pharmaceuticals;Elisa Kit-Rat Elisa Kit;6893-02-3 |
| Mol File: | 6893-02-3.mol |
3,3',5-Triiodo-L-thyronine Chemical Properties
| Melting point | 234-238 °C(lit.) |
| alpha | 23 º (c=2 in ethanol) |
| Boiling point | 232°C (rough estimate) |
| density | 2.2155 (estimate) |
| Fp | 9°C |
| storage temp. | -20°C |
| solubility | DMSO (Slightly), Methanol (Very Slightly) |
| pka | pKa 8.5 (Uncertain);8.4 (Uncertain);8.45 (Uncertain) |
| form | powder |
| color | Off-white to pale yellow |
| biological source | synthetic (organic) |
| Optical Rotation | [α]25/D +23.0°, c = 2 in 1 N HCl: ethanol, 1:2 |
| Water Solubility | Insoluble in water, ethanol and propylene glycol. Soluble in dilute alkalies. |
| Sensitive | Light Sensitive |
| Merck | 14,5510 |
| BRN | 2710227 |
| Stability: | Light Sensitive |
| Major Application | clinical testing clinical testing |
| InChI | 1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1 |
| InChIKey | AUYYCJSJGJYCDS-LBPRGKRZSA-N |
| SMILES | N[C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C(O)=O |
| CAS DataBase Reference | 6893-02-3(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn,Xi,T,F |
| Risk Statements | 20/21/22-36/37/38-39/23/24/25-23/24/25-11 |
| Safety Statements | 36-26-36/37/39-45-36/37-16 |
| RIDADR | UN1230 - class 3 - PG 2 - Methanol, solution |
| WGK Germany | 3 |
| RTECS | AY6750000 |
| F | 8 |
| HS Code | 29225090 |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Aquatic Chronic 3 Flam. Liq. 2 STOT SE 1 |
| Hazardous Substances Data | 6893-02-3(Hazardous Substances Data) |
| Toxicity | LDLo oral in rat: 7500mg/kg |
| Description | Crystalline T3 (liothyronine sodium, Cytomel) has a rapid onset and short duration of action. It is thetherapy of choice when it is desirable to have rapid onset or cessation of activity, such as in patients withheart disease. |
| Chemical Properties | Off-White Solid |
| Originator | Cytomel,SKF,US,1956 |
| Uses | T3 or 3,3',5-Triiodo-L-thyronine is a thyroid hormone involved with many physiological processes in the human body including growth and development, metabolism, body temperature and heart rate. Free and total T3 serum levels are measured by LC-MS/MS for determination of hyperthyroidism caused by excess T3. This Certified Spiking Solution? is suitable for use as a starting material in preparation of linearity standards, calibrators, and controls for thyroid hormone testing methods by LC-MS/MS. |
| Uses | 3,3’,5-Triiodo-L-thyronine (Levothyroxine EP Impurity A) is one of the hormones produced by the thyroid gland that is involved in the maintenance of metabolic homeostasis. Also produced in peripheral tissues as the active metabolite of Thyroxine. |
| Uses | One of the hormones produced by the thyroid gland that is involved in the maintenance of metabolic homeostasis. Also produced in peripheral tissues as the active metabolite of Thyroxine. |
| Application | 3,3′,5′-Triiodo-L-thyronine (T3) is an endocrine hormone produced by the thyroid gland and is regarded as an active thyroid hormone at cellular level. Thyroxine (T4) serves as a precursor for T3 and is generated in extrathyroidal tissues. 3,3′,5-Triiodo-L-thyronine sodium salt has been used for inducing thyroid hormone manipulations in mice. It has also been used In cell culturing of hippocampal, retinal, proximal tubule and glomerular explant. |
| Definition | ChEBI: An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxie in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism. |
| Manufacturing Process | The 3,5-diiodo compound used as a starting material is a known material andmay be prepared by the method in British Patents 643,089 and 671,070 andin the Journal of the Chemical Society, London, 1949, page 3424. Synthesis: L-diiodo thyronine (1.05 g) is dissolved in ammonia (specificgravity 0.880) (40 ml) and methanol (40 ml) and iodinated slowly withshaking with N-iodine in KI solution at room temperature. After iodination,most of the ammonia and methanol are removed by evaporation underdiminished pressure, water is added to the original volume, the solution isheated to 60°C and brought to pH 4 with hydrochloric acid. A crystallineprecipitate is obtained which after cooling to room temperature is collectedand washed with water. At this stage, the crude triiodo thyronine iscontaminated with thyroxine and a little unchanged diiodo thyronine. Purification: The crude precipitate is dissolved in boiling 2N HCl (300 ml) andfiltered from the relatively insoluble thyroxine hydrochloride. The hot filtrate isbrought to pH 4 with 5N NaOH and triiodo thyronine again separates; afterchilling at 0° to 4°C it is collected, washed with water and dried. The yield oftriiodo thyronine is 70 to 75% of the theoretical. This triiodo thyronine stillcontains some thyroxine (about 10%). The final purification consists of chromatographic separation of thyroxine andtriiodo thyronine on a kieselguhr column using 20% chloroform in n-butanolequilibrated with 0.5N NaOH as the developing solvent. 80 to 100 mg triiodothyronine is purified during each run on a 50 g kieselguhr column. Pure Ltriiodo thyronine has MP 236° to 237°C (dec.) and [α]D29.5° = +21.5 in a4.75% solution in a mixture of 1 part of N HCl and 2 parts of ethanol.Liothyronine is commonly used as the sodium salt. |
| Brand name | Triomet-131 (Abbott);Tri-Thyrotope (Bristol-Myers Squibb). |
| Therapeutic Function | Thyroid hormone |
| Biological Activity | 3,3′,5′-Triiodo-L-thyronine (T3) increases the rates of protein synthesis, stimulates the breakdown of cholesterol and effects embryonic development. In cell culture, T3 regulates cell differentiation and protein expression. The interaction of T3 with nonhistone proteins in the chromatin initiates the thyroid hormone activity. Thyroid hormones regulate the differentiation and development of tissues and affect a number of metabolic processes. The level of circulating T3 hormone is reduced in hypothyroidism. |
| Biochem/physiol Actions | 3,3′,5-Triiodo-L-thyronine also referred to as O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine or T3 is the biologically active thyroid hormone. In hypothyroidism pateints, triiodothyronine enhances mood and neuropsychological function. The product also positively regulates the hepatic FGF21 expression and stimulates the metabolic breakdown of glucose, fats, and proteins by enhancing the levels of numerous metabolic enzymes such as hexokinase, liver glucose 6-phosphatase as well as mitochondrial enzymes for oxidative phosphorylation. Additionally, the product facilitates the normal body growth in children and is pivotal for central nervous system maturation in foetus. |
| storage | -20°C |
| Purification Methods | Likely impurities are as in thyroxine. Purify it by dissolving in dilute NH3 at ~20o, then crystallise it by addition of dilute acetic acid to pH 6. Alternatively 35g are purified by dissolving it in a mixture of EtOH (250mL) and 2N NaOH (100mL), then hot 2N HCl is added to the boiling solution until the pH is 4-5. After cooling for a few hours, the solid is filtered off and dried in a vacuum [m 233-235o(dec)]. [Chambers et al. J Chem Soc 2433 1949, Beilstein 14 III 1566, 14 IV 2373.] |
3,3',5-Triiodo-L-thyronine Preparation Products And Raw materials
| Raw materials | iodine-->3,5-Diiodo-L-thyronine |
